Organic chem

[bec]

I'm having trouble with finding reaction pathways...

For example, finding a reaction pathway for the reaction of ethene to produce ethylamine.

I don't really even know where to start to be honest - i was thinking ethene--> ethane--> ethylamine, but i don't know the conditions of the substitution reaction b/ween ethane and NH3 that could produce ethylamine, or even if that is possible...

can anyone explain this to me?

[polky]

Well how I do it is I draw out the structure of what you have and what you want to get.  I can't picture stuff in my head, so by drawing it out I can figure out what I need to do (Eg. break the double bond between the two carbons).

How I would do it is ethene -> ethanol (through addition of H2O) -> ethylamine + H2O (through the addition of NH3, the OH in the ethanol gets substituted for NH2).

I don't know if that's the preferred pathway, but yeah.

Also, catalysts need to be used.  For ethene to ethanol, I think the catalyst is H3PO4, and from ethanol to ethylamine+water... I don't know xD.  My textbook says alumina!

I don't know if that helped at all but I hope it did!

[bec]

hmm that helps a bit, but i think what i need is some kind of list of what produces what

eg. amines can be formed through substitution reactions between ammonia and alkanol; alkanols can be formed through addition reactions of alkenes or substitiution reactions of chloroalkanes

i only just found those two "rules" but i'm going to look for more.
if anyone wants to contribute to my list......

[Mao]

generally:

alkane + chlorine -(UV LIGHT)-> chloroalkane

chloroalkane + sodium hydroxide -> alkanol

alkanol + ammonia -> amine

EDIT: its approved =)
http://notes.vcenotes.com/?step=download&action=feedback&id=70
this has got the pathway condensed from 4 textbooks =)

[bec]

wow that sounds amazing...you couldn't send it to me could you? can you attach files to personal messages?

[Mao]

*deleted*

EDIT: its approved =)
http://notes.vcenotes.com/?step=download&action=feedback&id=70

[bec]

that's amazing, thanks so much!
i didn't realised you'd already attached it haha

[lanvins]

ester formation question?

1. Write the formula of the alkanol and carboxylic acid used to make the following ester; CH3CH2COOCH2CH3

for the alkanol i got CH3CH2CH2OH

for the carboxylic acid i got CH3CH2COOH

but the book says that wrong, what should i do?

[Mao]

CH3CH2COOCH2CH3

looking at that carbon:

it is bonded to a CH2 group to the left (1 bond)
and two oxygens on the right (one double, one single)
thats a total of four bonds, therefore, it belongs to the carboxylic acid.
that is, you should get propanoic acid

the chain that remains has two carbons, which makes ethanol, not propanol.

[lanvins]

oh i think i get it now, thanks